Fullerene Building Blocks with Tailor-Made Solubility and New Insights into Their Hierarchical Self-Assembly

Perez-Ojeda Rodriguez ME, Wabra I, Böttcher C, Hirsch A (2018)

Publication Status: Published

Publication Type: Journal article, Original article

Publication year: 2018

Journal

Chemistry - A European Journal Wiley

Publisher: WILEY-V C H VERLAG GMBH

Book Volume: 24

Pages Range: 14088-14100

Journal Issue: 53

DOI: 10.1002/chem.201803036

Abstract

Herein, the synthesis of fullerene derivatives with adjustable polarities and lyotropic aggregation properties is reported. The polarity range spans from superhydrophobic to hydrophilic, while simultaneously providing a further reactive position with a view to graft them onto other materials. The synthetic strategy relies on a selective protection with an isoxazoline moiety. The remaining octahedral positions were further functionalized with the desired groups to tune their solubility, yielding mixed [5:1] hexakisadducts. The subsequent deprotection by clean photolytic reaction led to fullerene pentakisadducts with an incomplete octahedral addition pattern, which are useful forerunners for the synthesis of building blocks. Their hydrophobic/hydrophilic behavior has been characterized both in solution and surface through octanol/water partition coefficients (log P) and contact angle measurements. Furthermore, these derivatives can form supramolecular constructions which have been studied by dynamic light scattering (DLS) and cryo-TEM.

Authors with CRIS profile

Maria Eugenia Perez-Ojeda Rodriguez Lehrstuhl für Organische Chemie II Isabell Wabra Lehrstuhl für Organische Chemie II Andreas Hirsch Lehrstuhl für Organische Chemie II

Involved external institutions

Freie Universität Berlin DE Germany (DE)

How to cite

APA:

Perez-Ojeda Rodriguez, M.E., Wabra, I., Böttcher, C., & Hirsch, A. (2018). Fullerene Building Blocks with Tailor-Made Solubility and New Insights into Their Hierarchical Self-Assembly. Chemistry - A European Journal, 24(53), 14088-14100. https://doi.org/10.1002/chem.201803036

MLA:

Perez-Ojeda Rodriguez, Maria Eugenia, et al. "Fullerene Building Blocks with Tailor-Made Solubility and New Insights into Their Hierarchical Self-Assembly." Chemistry - A European Journal 24.53 (2018): 14088-14100.

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